


Three is Company

by fangirlingtodeath513



Series: Writers of Destiel Challenges [3]
Category: Supernatural
Genre: Anal Fingering, Anal Plug, Anal Sex, BDSM, BDSM Scene, Blindfolds, Blow Jobs, Bondage, Come Marking, Come Swallowing, Dirty Talk, Dom/sub, Dom/sub Play, Dominant Benny Lafitte, Dominant Castiel (Supernatural), Double Anal Penetration, Hand Jobs, Handcuffs, M/M, Marathon Sex, Oral Sex, Overstimulation, Polyamory, Praise Kink, Punishment, Rope Bondage, Sub Dean, Submissive Dean Winchester, Threesome - M/M/M, Vibrators
Language: English
Status: Completed
Published: 2019-06-03
Updated: 2019-06-03
Packaged: 2020-03-20 16:47:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,585
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18996598
Author URL: https://archiveofourown.org/users/fangirlingtodeath513/pseuds/fangirlingtodeath513
Summary: With a new toy on hand and two boyfriends willing to spend the entire day fucking him, Dean's got it made. If he can just make it through their scene, he'll get the reward of a lifetime.





	Three is Company

**Author's Note:**

> This was written for the Lusty Lexis challenge over in the Writers of Destiel discord. The prompt was "unique butt plugs". 
> 
> Thank you to the lovely Gii ([tumblr](https://gii-heylittleangel.tumblr.com/))([ao3](https://archiveofourown.org/users/heylittleangel/pseuds/heylittleangel)) for beta reading this fic for me!

Dean finishes the remainder of his lunch, swirling the water around his half-full glass. He’s buying himself time, but based on the looks on Cas and Benny’s faces, it ain’t subtle and it ain’t working. They’ve both crossed their arms and Castiel has an eyebrow cocked. Dean’s been with them long enough to know that now is his time to back out, if he wants to. He finishes his glass of water in a few gulps, letting out a nervous breath. “Alright, let’s do this.”

 

“Are you sure?” Cas asks, his voice soft and his head tilted to the side. It’s a quirk Cas doesn’t even realize he has, but Dean’s found it adorable since the minute he first saw it.

 

“I’m positive,” Dean answers firmly, much more firmly than he actually feels. He’s a ball of nerves and he feels like he might just vibrate apart from the inside based on how fast his nerve endings are firing. He’s jittery—he’s been jittery all day. It’s not the bad kind of nerves, he’s _beyond_ excited for this. But it’s also the first scene of this magnitude that the three of them will do together and he’s kinda scared he’s gonna fuck it up.

 

Benny chuckles, leaning across the table to lay his hand over Dean’s, giving it a gentle squeeze. “Relax, Dean. We may be in control, but you hold all the cards. You don’t want this, it doesn’t happen.”

 

“I want it,” Dean insists. “I’m just nervous. We haven’t done a long scene like this in a while, and even less with both of you domming me. I’m just scared I’m gonna fuck up.”

 

Castiel snorts, then quickly slaps a hand over his own mouth. “I’m sorry, Dean. I don’t mean to laugh, but you know you’re not actually capable of fucking anything up, right?”

 

Dean frowns. “No. I could fuck a lot up.”

 

Castiel shakes his head. “Dean, no. The only thing you could possibly do wrong is not use your safe word, but you’ve used it more than a few times with both Benny and myself, I know this won’t be any different. You’re quite adept at following rules, and Benny and I can both read you well enough that we’ll be able to change course before you need to safe word.”

 

Cas is assuaging Dean’s nerves, as usual. Drawing in a steadying breath, Dean nods. “Alright. Let’s go, then.”

 

Benny smiles. “Go on, cher. Cas and I will clean up lunch and then we’ll be in.”

 

“Clothes folded on the dresser and kneeling next to the bed, love,” Cas murmurs, fingers brushing through Dean’s hair as he makes his way to the sink. Nodding, Dean pushes himself away from the table and heads for their bedroom, determined to use the few minutes of alone time he’ll have to calm himself down.

 

He’s not scared of what they’ve got planned. They’d talked about it for weeks before they all finally sat down and agreed on a date. Cas had ordered two new toys and Dean spent the last week working himself up to bigger and bigger toys. He’s _excited_ for that part of it.

 

Pushing all the other feelings aside, Dean lets the excitement wash over him as he strips and neatly folds his clothes, leaving them on top of the dresser they all share. He grabs his pillow off the bed and sets it on the floor at the foot of the bed, kneeling on it. He shuffles around until he’s comfortable, sitting back on his heels with his hands resting on his thighs. He closes his eyes and bows his head, letting out a slow breath that takes all the fear and nervousness with it, leaving him buzzing with excitement.

 

Dean’s not sure how long he kneels there like that. He can’t hear anything from the kitchen in this part of the house, so he only hears the soft steps of Cas and Benny when they’re near the bedroom. He stays still, already determined to be good for them.

 

“Now, ain’t that a beautiful sight?” Benny whistles, fingers carding through Dean’s hair. “What a good boy for us already.”

 

Dean shivers, eyes fluttering open. “Thank you, sir,” he murmurs, leaning into Benny’s warm hand.

 

“Whatcha think, Cas? Shall we?”

 

Dean can practically picture the smirk on Cas’s face, though he doesn’t dare turn to look. He hasn’t been given permission to move from his position.

 

“I think we’ve tortured him enough the past week with the anticipation,” Castiel replies. He sounds farther away then Benny, maybe still in the doorway. “Frankly, I don’t really want to wait any longer either.”

 

Benny chuckles, tapping Dean’s shoulder lightly as he steps back. It’s Dean’s cue to move, so he shuffles off the pillow and pushes himself to his feet, biting his lip when he sees Cas holding their two new toys, his eyes scanning the length of Dean’s body. When their eyes finally meet, Dean finds something he can only call hunger there.

 

They’ve developed a silent language between the three of them. They’ve been together for nearly five years now, and friends for a long time before that. The three of them are at a point now where a certain look is more than enough to tell Dean what to do or where to move. It comes in handy most of the time, though sometimes Dean longs to hear the orders out loud. Cas and Benny are usually pretty good about that, thankfully. Without either of them having to ask, Dean takes their clothes and folds them, setting them in neat piles next to his own. In the meantime, Cas and Benny head straight for the bed, stripping the blankets off and switching their normal fitted sheet for a rubbery one they’d gotten specifically for scening. It’s fluid proof, which makes cleanup afterward a hell of a lot easier, especially considering Dean’s pretty useless for cleanup after scenes.

 

Cas moves the blankets to the corner of the room where they’ll stay clean, tossing the new toys on the bed. He digs through his bedside table, tossing a bottle of lube on the bed, along with a few lengths of rope and a blindfold. Dean’s practically dancing with excitement as he watches, despite the fact that he knows everything they’ll be doing in this scene. Benny’s smirking at him, obviously able to tell just how excited Dean is.

 

Finally, Castiel turns his attention to Dean and crooks a finger at him, pointing to the bed. Nodding, Dean crosses the room quickly and settles in the center of the bed, glancing between Benny and Cas.

 

“Your safe word?” Cas prompts, fingertips skimming down Dean’s side, leaving a trail of goosebumps in their wake.

 

“Impala,” Dean murmurs, swallowing thickly when he sees the pleased look on Cas’s face.

 

“Good boy. Shall we begin?”

 

“Yes, please, sir.”

 

Their scenes typically have a dynamic agreed upon beforehand. Dean’s always a submissive, and Cas is always a dominant. Benny’s a switch, which works perfectly for the three of them. They can plan all manner of scenes—Dean being submissive to both Castiel and Benny, Dean and Benny being submissive for Castiel, and the gray area they often fall into, much like this particular scene. Benny is still Dean’s dom, though Benny defers to Castiel’s judgment. Benny doesn’t usually give orders when he’s floating around in the gray area, and Cas doesn’t typically give him orders. It’s taken some work to get comfortable with the arrangement, but Dean wouldn’t change it for anything. What they have is perfect.

 

The two of them take their time tying knots in the ropes around his wrists, tight enough that he won’t be able to get out but loose enough that it won’t cut off circulation. The other ends of the ropes are tied to metal loops they’d attached to the headboard years ago, specifically for this reason. Dean gives the ropes a tug, letting out a breath and nodding. Not too tight, but tied well enough that no matter how much he struggles during the first part of their scene, he won’t be able to escape.

 

“Good boy,” Castiel purrs, fingers carding through Dean’s hair for a moment. His thumb swipes along Dean’s cheekbone and then he’s sliding the blindfold over Dean’s eyes, lifting Dean’s head to slide the elastic around it. “We won’t be using your mouth for this part, so you’re free to safe word if you need to. If you need a moment, or you need to see us, say yellow. Understand?”

 

Dean shivers at the commanding shift in Castiel’s tone, nodding. “Yes, sir. I understand.”

 

“Perfect, as always,” Castiel hums, fingers skimming over one of Dean’s nipples. “Ready to begin?”

 

“Yes, sir,” Dean murmurs, already shaking with anticipation.

 

Benny smirks, crossing his arms over his chest. “Always am.”

 

Nodding, Castiel kneels on the bed, just to Dean’s right, fingers toying with Dean’s nipples. Dean can hear faint footsteps, Benny’s heavy footfalls muffled by their plush carpet. The bed dips and then Benny’s kneeling between Dean’s legs, fingertips skimming from his ankle all the way up to the crease of his leg. Dean lets out a slow breath, squirming as Castiel’s mouth closes around one of his nipples, teeth gently tugging the bud. Benny follows suit, fingertips teasing Dean’s inner thighs.

 

Dean’s always had sensitive nipples, especially when he’s incredibly turned on, and Cas and Benny have learned to use that to their advantage over the years. They have him panting within a few minutes, begging them to move on. They don’t. They keep teasing his nipples until he’s covered in a thin sheen of sweat, tugging at the ropes binding his wrists.

 

“Please, please, i-it’s too much, sirs, _please_ , fuck!”

 

He can feel Castiel smile against his chest, which is all kinds of hot and frustrating. Begging was a mistake, Dean knows that. It only ever gets him more of what he’s begging for them to end, which is exactly what happens this time. Cas and Benny double their efforts, fingers skimming Dean’s overheated skin as they suck and bite at his nipples, hands on his stomach to keep him still. Dean rocks his hips up, but there’s nothing for him to rut against, just the empty, cool air of their bedroom. Groaning breathlessly, Dean struggles against the ropes, whimpering softly when Cas and Benny both pull away abruptly. He instantly falls still, mind running through everything to make sure he hadn’t disobeyed an order.

 

“You haven’t done anything wrong, love,” Castiel says softly, fingers gently brushing against Dean’s knee. It’s creepy how well he can read Dean without a single word, frankly.

 

Dean strains his ears to hear what’s going on, but he can’t make anything out. Benny hasn’t moved from his spot between Dean’s legs, and Castiel is still hovering at Dean’s side. One of Benny’s large, warm hands wraps around Dean’s cock, giving it a few quick strokes.

 

“You tell us how you wanna do this, cher. Cas and I are gonna make you come until you can’t do anything but sob our names, and then we’re gonna fuck you and make you come again.” Benny smirks at Castiel, shrugging. “Maybe a few times, if we’re feelin’ up to it. So do you want us to start with our hands or our mouths?”

 

Dean whimpers quietly at the image that puts in his head, biting his lip. “M-mouths, please, sir.”

 

Benny doesn’t waste any time swallowing Dean’s cock down to the root, one hand on Dean’s thigh while the other rubs the sensitive skin behind Dean’s sac. It leaves Dean breathless and squirming in less than a minute, pumping his hips up into Benny’s waiting mouth.

 

This is one thing they’ve never done before. Dean’s been edged by the two of them for hours, sometimes even entire days where he’s not allowed to come until the very end of the scene. Usually, it knocks him right out and he sleeps forever after that. This, though, _this_ they’ve never done. Dean’s not entirely sure how well he’ll be able to handle it, but he’s more than a little excited to try.

 

He comes down Benny’s throat the first time, head thrown back as a low moan escaped him. He can hear Castiel’s breathy chuckle somewhere to his left.

 

“That’s only your first one, love. We’ve got much more in store.” He pets Dean’s hair lightly, switching places with Benny and wrapping a warm hand around Dean’s softening cock. “Think you’ll be able to get hard for me again, Dean? Be my good boy?”

 

Dean whimpers softly, rocking up into Castiel’s tight fist, shivering as the tingly feeling of oversensitivity sets in. “I-I’ll try, sir,” he gasps out, moaning breathlessly as Castiel nips at the insides of his thighs.

 

The minute Cas feels Dean getting hard again, he swallows him down just as quickly as Benny had, pulling out every move he has to get Dean to come in less than two minutes, crying out something that barely resembles Castiel's name. Castiel doesn’t release him though, instead just pulls back and teases the head of Dean’s cock with his unfairly talented tongue, wracking an overwhelmed sob from Dean’s chest. He grabs onto the ropes tighter, trying to use them to ground himself. He’s already starting to lose it and he’s only come twice. This doesn’t bode well.

 

He’s barely fully hard before he’s coming in Castiel’s mouth again, shuddering through the intense wave of pleasure-pain. He pants out a, “please, sir, _fuck_ ,” though even Dean isn’t sure whether he wants Castiel to stop or continue.

 

Cas and Benny work him for what feels like an eternity, swapping off every few minutes. Dean swears he comes another dozen times before the two of them finally slide off the bed and untie his hands, thumbs smoothing over the raw skin gently.

 

“How’re you doing, love?” Castiel asks softly, gently sliding the blindfold up to rest on Dean’s forehead. “Do you need a minute?”

 

Dean nods shakily, blinking a few times as his eyes adjust to the light. “Y-yes please, sir, just t-to catch my breath.”

 

“Of course, my love. Can you sit up for me?”

 

Dean nods again, letting Castiel help him into a sitting position, sipping at the glass of water Benny offers him. Cas wipes Dean’s cheeks gently, setting the blindfold aside.

 

“Finish that glass and then we’ll continue, deal?”

 

Dean smiles softly and nods, leaning against Castiel as he sips the ice cold water. Benny takes the glass once it’s empty, setting it on the bedside table. “Ready to go, cher?”

 

“Yes, sir,” Dean murmurs, clearing his throat. It’s a little scratchy already, which means it’ll be deliciously sore tomorrow. Although, given how the scene’s going, it won’t be the only thing sore tomorrow.

 

Castiel nips Dean’s earlobe, smirking. “How about we try one of our new toys, love? You’ve been so good, I’ll even let you pick which one.”

 

Dean squirms, biting his lip. “The plug, please. Wanna save the other one for somethin’ else.”

 

Benny smirks, the look on his face telling Dean that Benny is _well_ aware of what that something else is. He feels his cheeks heating up, so he turns and buries his face in Castiel’s chest. Castiel laughs quietly, hand brushing up and down Dean’s back lazily. “I’m sure Benny has an old pair of cowboy boots lying around somewhere, and I should be able to steal a couple of white coats without anyone noticing.”

 

Dean shivers at the image that puts in his head, nodding quickly. “Fuck, yes _please_ …”

 

Benny laughs. “Another time, Dean. Whatcha think, Cas? Bend him over the bed and tie him up? Leave him wide open, just waiting for us to take turns?”

 

Dean feels rather than hears the pleased rumble in Castiel’s chest. “Sounds like a phenomenal idea to me.” He cards his fingers through Dean’s hair, pressing a light kiss to his forehead. “How’re you doing, my love?”

 

“I’m better, sir. The water helped. Can we keep going?”

 

He sees Cas’s eyes darken, then flick to where Benny’s standing. “Maybe the leather cuffs this time, so he won’t chafe so much.” He nudges Dean off his lap as Benny goes to collect the leather cuffs, grabbing the blindfold and slipping it down over Dean’s eyes. He guides Dean off the bed, smirking as Benny returns with the leather cuffs.

 

Dean gasps as Castiel’s hand closes around the back of his neck, shoving him down against the mattress, chest and face pressed into the rubbery sheets. His breath is hot on Dean’s ear when he speaks, “Don’t you dare move from this position. You’re ours, now. The minute you move your feet or grind back against either of us without permission is the minute Benny and I pull ourselves away. And if you can’t be a good boy… well, maybe I’ll just have to take that blindfold off and let you watch Benny fuck me.”

 

Dean whimpers, fingers digging into the sheets beneath him. Cas and his ridiculously filthy mouth will be the death of him, he’s convinced. “W-what if I need to shift my weight or somethin’?”

 

“You ask permission first, of course.” Castiel’s hand slides into his hair, gripping it so tightly that tears prick in the corners of Dean’s eyes. “Do. Not. Move.”

 

Forcing back the shiver threatening to run through him, Dean sucks in a sharp breath. “I won’t, sir.”

 

Castiel lets go of his hair, taking one pair of cuffs from Benny. Dean’s hands are quickly cuffed, one to the headboard and one to the back of the bench at the end of their bed. The leather cuffs are far more comfortable than the rope, so Dean lets himself sink deeper into the mattress as Benny’s fingers glide over his entrance, already slick with lube.

 

Benny doesn’t waste any time sliding the plug into him. They’d picked out the toy together, specifically for this purpose—it’ll keep Dean spread wide open even when they’re not fucking him, and he won’t be able to keep the cum from dripping down his thighs. Dean’s practically drooling at the thought and they haven’t even started yet.

 

It’s a thick silicone, thick enough that it won’t bend under the pressure of Dean squeezing around it, but wide enough that both Benny and Castiel’s cocks can fit through. Under normal circumstances, it would’ve been too big for Dean to wear for long, but he’s been working himself up to bigger and bigger toys over the week, so this is nothing compared to them.

 

“That’s a pretty sight,” Benny rumbles, fingers digging into Dean’s left hip. “You wanna go first, Halo?”

 

Castiel chuckles. “Go ahead, I’ve been dying for his mouth all week.”

 

Dean pouts. If Cas had just _asked_ , Dean gladly would’ve blown him earlier in the week. Still, he won’t complain about the opportunity to suck Castiel’s cock. Benny’s hands grip onto Dean’s sides, his cock brushing against Dean’s ass and leaving a trail of precum. Dean can feel Castiel settling onto the bed, then he gets a tap to his chin.

 

“Lift your head up, love,”

 

Dean hums, shifting himself until Castiel’s settled, letting his mouth fall open as Castiel guides his cock inside with a groan.

 

“If you need to safe word, it’s two snaps. Snap once if you understand.”

 

Dean swirls his tongue around Cas’s cockhead, snapping once. Satisfied, Cas pushes his hips up, driving deeper into Dean’s mouth with a soft grunt. Dean loosens his jaw, letting Castiel thrust a few times before he actually starts to suck his cock, tongue dipping into Cas’s slit when he pulls back.

 

The minute Dean gets a rhythm going is the exact minute Benny finally pushes into him and Dean instantly regrets this toy purchase. It’s going to be torture. The toy had been molded so there was a ridge that, if place properly, could sit right over the prostate and stimulate it constantly. At the time, Dean thought it would be a great feature, but now all he can think about is how intense it’ll be while he’s being fucked.

 

He groans around Castiel’s cock, which has Cas gripping Dean’s hair tightly as a strangled moan escapes his lips. “ _Fuck_ , Dean.”

 

Benny chuckles, brushing his thumb along Dean’s stretched rim. “Let’s see how well he can blow you while he’s getting fucked. What do you think about a little wager?”

 

Castiel pants softly, struggling with the effort to keep from pushing into Dean’s mouth. “What kind of wager?”

 

Benny hums. “If he gets you to come before me, he gets a reward later. If he doesn’t, he’ll have to sit here with a vibrator in him instead of us.”

 

Dean whimpers quietly, struggling to keep himself from objecting. He doesn’t _want_ a vibrator, especially when he has two men entirely willing to fuck him.

 

Castiel chuckles, tugging Dean’s hair until he’s forced to release Castiel’s cock. Dean doesn’t bother to hide his pout. “What do you think, love? Think you can get me off before Benny?”

 

Dean’s confident that, under normal circumstances, he’d be able to get Castiel off quickly. But with Benny fucking him at the same time? “I’ll try, sir.”

 

“That’s my good boy,” Castiel purrs, guiding Dean back down onto his cock.

 

Benny doesn’t even give him a chance to get situated on Cas’s cock, he just digs his fingers into Dean’s hips and starts pounding into him, the sounds of skin slapping skin and his harsh breaths quickly filling the room. Determined, Dean focuses all of his attention on worshiping Castiel’s cock in every way he can—tonguing the slit, teasing the vein on the bottom, letting Cas fuck down his throat.

 

It’s a close call, but Cas comes half a minute before Benny does, hand gripping the back of Dean’s neck to hold him still as he spills down his throat with a grunt. Benny fucks Dean through his own orgasm, reaching a hand around to give Dean’s cock a few quick tugs. Dean comes with a strangled moan around Castiel’s cock, barely able to keep from curling his toes from the pleasure.

 

Castiel gently lifts Dean’s head off his cock, climbing off the bed as Dean catches his breath. “Good job, love. We’ll let you pick your reward later, hm?”

 

“Thank you, sir,” Dean murmurs, his voice raspy.

 

Benny pulls out gently, hand brushing up Dean’s back as he watches Dean try to clench around the emptiness. “Can’t wait to see you covered in our cum, cher. Gonna be such a pretty sight. Might even take a picture, if you’ll let me.”

 

Dean gasps softly. “Y-yes, sir, _fuck_ yes.”

 

Castiel chuckles, nails scratching down Dean’s back just hard enough to raise the skin. “You were awfully quick to answer that, love. Like the idea of us having a picture of you like that? Covered in our cum, so full of it you’ll be leaking it for days? Prove to everyone you’re ours?”

 

Dean whimpers quietly, every muscle in his body straining as he forces himself to keep from shivering. “Yes, sir,” he mumbles, thankful the blindfold hides most of his cheeks. Dean has no doubt they’re burning bright red at the moment.

 

Cas hums, smacking Dean’s ass sharply. “I’m going to get a glass of water for myself and Benny, and I’ll refill yours as well. In the meantime, Benny’s in charge. I can trust you to be good for him, right?”

  
“Of course, sir,” Dean answers immediately, biting his lip. He’s rarely left alone with Benny fully in charge like this, even if it’s for a little while.

 

“Good. I’ll be right back.” Castiel’s hand sweeps the length of Dean’s waist before his footsteps fade into the distance. Dean sucks in a sharp breath, smirking.

 

“Do you want to know what I’m going to pick as my reward, sir?” He purrs, grinning when he hears Benny’s weight shift behind him.

 

“Just because Cas ain’t here doesn’t mean you can suddenly get mouthy. Now hush, or I’ll put a vibrator in you and call it a night,” Benny replies easily, though his voice lacks the commanding tone Castiel usually has.

 

“You aren’t curious?” Dean whispers. He’s content to push the limits a little bit tonight, see just how hard he can bend them before he gets a stern warning.

 

“ _Dean_.”

 

Dean snaps his mouth shut. Benny’s clearly not in any mood to be prodded tonight, and Dean’s not about to lose the reward he’s been dreaming about for a long time now. No way. He stays quiet until Castiel returns, brows furrowing when Castiel uncuffs one of his wrists.

 

“Did I do something wrong, sir?”

 

“No, love.” He can hear the smile in Castiel’s words, which helps him relax. Benny helps him sit up, sliding the blindfold up to his forehead and handing Dean a glass of water.

 

“Drink up, cher. Cas’s turn next,” Benny says with a wicked smirk. He sits in the leather chair in the corner of the room, sprawling out and sipping at his water lazily. “Gonna be quite the show.”

 

Dean squirms, sipping from his own glass. The feeling of the plug holding him open is one of the weirdest things he’s ever felt, especially combined with the feeling of Benny’s cum dripping from his hole, no doubt making a mess of the bed.

 

Castiel takes Dean’s glass once it’s empty, setting it on the nightstand and waving a hand in Dean’s direction. Dean shuffles back to his original position, closing his eyes as Cas replaces the blindfold and cuffs his wrist once again.

 

He’s only barely settled onto the bed when Castiel pushes into him roughly, grinding the bump on the toy directly into Dean’s prostate. Dean jolts at the sensation, whimpering quietly.

 

Cas clicks his tongue, fingernails digging into Dean’s hips. “I thought I was clear when I said no moving, Dean.”

 

“I-I know. You were, sir, you just startled me. It won’t happen again, I promise.”

 

“You’re right, love, it won’t. Benny, will you grab a vibrator?”

 

Dean whines softly, squeezing his eyes shut tighter. “No, sir, _please_ , it was an accident. I won’t move again.”

 

Castiel hums, thanking Benny quietly. “I’ve taught you better than to have accidents, my love. Now I’m going to leave you here with this vibrator for fifteen minutes—" he pulls out of Dean, replacing his own cock with an already-buzzing vibrator, leaving it on the highest setting as he pushes it in all the way to the base, “—and I’m gonna go have some fun with Benny.” Castiel leans over Dean and he can feel Cas smirk as he nips at Dean’s earlobe. “Maybe we’ll even move the party to the bed so you can watch.”

 

Dean barely bites back a whimper, all of his energy redirected to the vibrator buzzing away in his ass, driving the nub on the toy into his prostate over and over again. “I-I’m sorry, sir, _please_ ,” he begs, moaning breathlessly when Castiel smacks his ass sharply.

 

“You knew the rules, boy. Take your punishment quietly or I’ll make it even longer,” Castiel growls.

 

Dean suppresses a shiver, taking a deep breath. He can do this, it’s only fifteen minutes. Besides, with the blindfold on, he won’t even have to see what Benny and Cas are doing. He just has to get through these fifteen minutes and then they can get back on track.

 

At least, that’s what he thinks. Castiel obviously has other ideas. He whips the blindfold off Dean’s face, smirking. “You didn’t really think I’d let you get away with just listening, did you? I know that wouldn’t be an effective punishment for you.”

 

Dean groans softly, resisting the urge to struggle against his cuffs. He’s not going to be a brat tonight. It’s only for fifteen minutes. It may be a torturous fifteen minutes, but he can get through it.

 

Castiel sprawls out on the other side of their California king, idly stroking his cock as he smirks lazily in Dean’s direction. Dean frowns. Is he just going to watch Cas get himself off? That won’t be so bad.

 

Benny kneels between Cas’s legs, already slicking his cock with lube once more, and then Dean’s brain finally clicks. He’s gonna have to sit here, utterly still with a vibrator buzzing against his prostate, and watch his boyfriends fuck. That is _so_ not fair. He’s only actually seen Cas and Benny fuck a handful of times, usually when they’re both drunk and handsy. He almost whines at the injustice of being tied down to the bed while the two hottest people in the world fuck right in front of him. _Not_ cool.

 

Castiel smirks as if he knows exactly what’s going through Dean’s head. Creepy part is, he probably does. He hooks his legs around Benny’s waist, giving a long, low groan as Benny pushes into him.

 

Dean doesn’t even realize that the strangled noise he hears comes from himself. Benny and Castiel both chuckle at him, though Castiel’s is a little more breathy.

 

“I was planning on tying you spread eagle and riding you while Benny fucked you, hence me being prepared already. I think you’ve lost that privilege, now.”

 

Dean whines quietly. Between Benny and Cas in front of him and the vibrator buzzing right against his prostate, Dean’s losing any semblance of self-control that he had. He’s still got a while to go, so he forces himself to focus on breathing. Castiel hadn’t said anything about not coming, so he breathes deeply and focuses on the vibrator, rather than the sight of them.

 

It doesn’t work. That’s not entirely surprising since the mere thought of them together had Dean drooling. He sinks deeper into the mattress, resigning himself to his punishment.

 

“Oh _fuck,_ Benny,” Castiel pants, his head thrown back and his eyes squeezed shut. Dean whimpers softly, tugging at the cuffs absentmindedly. He wants to touch, he doesn’t want to just sit here and watch.

 

If either of them notices, they don’t say anything, much to Dean’s relief. He doesn’t want any more time tacked onto his punishment.

 

He tries to filter out the sounds of their grunts and pleasured moans, but he can’t seem to tear his eyes away from them. Outside of their scenes, Castiel has no problem bottoming, but seeing it from this angle? He gets to watch every expression filter over Castiel's face, see the sweat beading at his temples, how the muscles of his thighs start to shake when he’s close…

 

Cas comes with a low moan, arched up against Benny. It’s a hell of a sight, and it has Dean coming on the floor only a second later, shuddering through what has to be his fifteenth orgasm of the night.

 

Castiel grins lazily, flicking his eyes over to Dean. “Why don’t you go finish in him, Benny? He looks like he could use a good fuck right now, maybe you can even wring another orgasm out of him.”

 

Dean whimpers, letting out a relieved breath when Benny removes the vibrator and clicks it off, setting it on the bed.

 

“If you can be good and keep still while Benny finishes, I’ll let you move as much as you want the rest of the night. Understand?”

 

“Yes, sir,” Dean stutters out, forcing himself to stay still as Benny pushes into him roughly, digging his nails into Dean’s hips. He doesn’t even get to adjust before Benny’s pounding into him, tugging his hips back roughly on every thrust. It doesn’t take him long to come, which is a relief. Dean isn’t sure how much longer he could’ve taken that stupid nub digging into his prostate. He takes a few breaths to steady himself as Benny pulls out, but he doesn’t get a chance to actually relax, because Benny’s cock is quickly replaced with Castiel’s. He shows no mercy, grinding into Dean until he’s sobbing from the oversensitivity of it all, scrambling for something to grab onto. He manages to wrap the metal chains of his cuffs around his hands, gripping so tightly that they leave marks on his palms.

 

He’s passed back and forth like that for another hour, Benny and Cas switching off after they come. By the time he finally gets a break, there’s a steady stream of their combined cum dripping down his thighs and he’s covered in a thin layer of sweat, his chest heaving. He vaguely registers the click of Benny’s phone as he takes a few pictures, making a mental note to look at those later.

 

The two of them uncuff him and slide the plug out gently, setting the messy toy on the bed. Dean’s coaxed onto his back and then into a sitting position. Benny rubs at his wrists gently while Castiel gets him to drink some water, smoothing his hair back gently.

 

“You did so well, sweetheart. Such a good boy for us, I’m so proud of you.”

 

Dean hums tiredly, sagging back against Benny as he downs the rest of the water in the glass. “Do I get my reward now?” he mumbles, eagerly taking the second glass of water that Castiel offers him.

 

“If you want to, love, sure. I’ll take a rain check if you’re too tired, though.”

 

Dean shakes his head, frowning. “Nuh uh. I want to. Please?”

 

Castiel smiles, leaning down to kiss Dean gently, thumb stroking Dean’s cheekbone. “Of course, my love. What do you want as your reward?”

 

Dean grins wickedly, glancing between Benny and Cas. “Want you to fuck me.”

 

Benny raises an eyebrow, chuckling. “Been doin’ that all night, cher. You want another round?”

 

Dean shakes his head, handing his empty glass to Castiel. “No, no, I want you _both_ to fuck me.”

 

Benny stares at him, confusion evident on his face, but Dean can see the moment Castiel realizes what he’s asking for. His eyes darken and his throat bobs as he swallows thickly, tongue darting out to lick his lips. “You want us to fuck you at the same time? You sure you’re ready for that, Dean? We’ve never tried it before.”

 

Dean scoffs. “I’ve been prepping myself all week, and you had a plug keeping me open for the last hour. I can handle it.”

 

Castiel watches him for a moment before his eyes flicker to Benny. “Sounds like an excellent reward to me.”

 

Benny nods his agreement, smirking. “Hell yeah. Let’s do this.”

 

Dean grins, shifting to straddle Benny’s lap. “Wanna ride you, please?” he murmurs, leaving a trail of hot, wet kisses down the side of his neck. Benny shivers, grabbing Dean’s ass as he nods.

 

“Set us up however you want, cher. It’s your reward.”

 

Dean hums, pushing against Benny’s chest until he lays back against the bed, lowering himself onto Benny’s cock with a satisfied groan. “Wanna ride you, then Cas can fuck me from behind.”

 

Castiel chuckles, his thumbs already brushing over Dean’s rim where it’s stretched around Benny’s cock. “Given this a lot of thought, have you?”

 

Dean blushes, hiding his face in Benny’s chest as he shrugs. Castiel laughs, squeezing Dean’s hip gently.

 

“I didn’t mean that like it was a bad thing, love. You can share fantasies like this with us, though.”

 

“I know,” Dean mumbles, grinding down on Benny’s cock. He inhales sharply when Cas presses a finger in beside Benny’s cock, biting his lip. “More, I can take more. Please, Cas…”

 

Castiel hums, slipping a second finger in, then a third, easily rocking them in time with Benny’s lazy thrusts. The fourth finger is the one that tips over into the pain side, though it’s a barely-there burn that dissipates within a minute. Panting, Dean digs his nails into Benny’s chest and grinds down onto his cock and Castiel’s fingers.

 

“Cas, _please_ ,” Dean groans, eyes fluttering shut as Castiel withdraws his fingers. There’s a moment where the entire room is silent, and then the blunt head of Castiel’s cock his brushing against Dean’s ass, sliding into him inch by inch. It’s fucking exhausting, between trying to keep himself from scratching at Benny’s chest and remembering to breathe. Holy _fuck_ is it amazing, though.

 

He collapses against Benny’s chest when Castiel finally bottoms out, barely biting back a sob at how good it feels. “Oh my god, I-I…. oh _fuck_!”

 

Benny chuckles, looping an arm around Dean’s waist. “Agreed. How do you want us to move, baby?”

 

Dean whimpers, sucking in a shaky breath. “I-I don’t know, just fucking move, I’ll figure it out in a sec.”

 

Castiel laughs, gripping Dean’s hips tightly as he finally starts to move, timing his movements to mirror Benny’s. After a minute, Dean lifts his head up just far enough to shake it. “O-opposite, fuck, need you to try it opposite of each other,” he manages to pant out, grabbing Benny’s shoulders tightly. The two of them finally get a rhythm going and Dean thinks he might die right there. Wouldn’t be a bad way to go, frankly. He can hardly concentrate, so he just gives up and lets the two of them take over.

 

It’s overwhelming in the best way. It’s the fullest he’s ever felt, and the fact that he can actually fit both of them at once is so insanely hot. He nuzzles against Benny’s neck, breath harsh as they fuck him. Neither of them holds back, either. Castiel’s nails are undoubtedly leaving crescent-shaped indents on his hips, and Dean’s positive he won’t be able to so much as breathe tomorrow without feeling both of them like this.

 

He feels rather than hears when Castiel gets close. His fingers dig into Dean’s hips just a bit more and he starts to fuck Dean harder, his hips smacking against Dean’s ass on every thrust. Benny’s not much farther behind if his ever-tightening grip around Dean’s middle is anything to go by.

 

The minute Castiel comes, Dean’s gone. Dean comes with a muffled sob against Benny’s neck, his cock untouched between him and Benny, who comes only a few seconds later. Cas and Benny work themselves through their orgasms, loosening their hold on Dean in the process. Slowly, Castiel slides out with a sigh, helping Dean up and off Benny’s cock, letting him sprawl out on the bed. Cas cleans the three of them up as best he can, nudging Dean and Benny off the bed so he can toss the sheets in the laundry. Benny remakes the bed with their usual sheets, making Dean drink a glass of juice before he’s allowed to nestle into the covers.

 

That’s how Castiel finds them ten minutes later, sprawled in the middle of the bed with the blankets slung low over their hips. Dean’s sound asleep on Benny’s chest, looking more relaxed than he has in months. Castiel climbs in carefully, though he can’t avoid jostling the bed. Dean rolls to him almost immediately, pulling him into a sloppy kiss that’s more of a grin than anything.

  
“That was fuckin’ awesome,” he mumbles, snuggling back against Benny’s chest and tugging Castiel in behind him. “We’re definitely doing that again.”

 

Castiel laughs softly, brushing gentle fingers through Dean’s hair. “Whatever you want, Dean. Sweet dreams.” He leans over Dean to kiss Benny lightly, sliding an arm around Dean’s waist. “Goodnight, both of you. I love you,” Cas mumbles into the darkness, sated and warm next to his two lovers.

**Author's Note:**

> Find **this fic** on [Tumblr](https://fangirlingtodeath513.tumblr.com/post/185327144544/three-is-company-a-deancasbenny-fic-for-week-3) and [Pillowfort](https://www.pillowfort.social/posts/687006)  
>   
> Find **me** on [Tumblr](https://fangirlingtodeath513.tumblr.com/) and [Pillowfort](https://www.pillowfort.io/fangirlingtodeath513)  
>   
>  **Please don’t post my works anywhere without my permission.**


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